# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1454099'
_audit_update_record             
;
2016-02-17 deposited with the CCDC.
2016-04-29 downloaded from the CCDC.
;
_vrf_PLAT201_1                   
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         36 Report
RESPONSE:
	A structure model with anisotropic displacement parameters for C, N and O 
	atoms did not result in a significant improvement
;

_vrf_PLAT434_1                   
;
PROBLEM: Short Inter HL..HL Contacts
RESPONSE:
	These interactions and their analysis are the motivation of our study
;

_audit_creation_method           SHELXL-2012
_chemical_name_systematic        'compound 1'
_chemical_name_common            
;
 L-tyrosiniumpolyiodide hydrate
;
_chemical_melting_point          ?
_chemical_formula_moiety         '4(C9 H12 N O3), I16, H2 O'
_chemical_formula_sum            'C36 H50 I16 N4 O13'
_chemical_formula_weight         2777.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   11.8549(13)
_cell_length_b                   16.4789(18)
_cell_length_c                   17.3200(19)
_cell_angle_alpha                90
_cell_angle_beta                 101.091(2)
_cell_angle_gamma                90
_cell_volume                     3320.4(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9589
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      27.95

_exptl_crystal_description       plate
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.778
_exptl_crystal_F_000             2492
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    7.507
_shelx_estimated_absorpt_T_min   0.212
_shelx_estimated_absorpt_T_max   0.521
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.350
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Incoatec microsource'
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_measurement_device_type  'Bruker D8 gonimeter with APEX CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            45294
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.198
_diffrn_reflns_theta_max         28.266
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             16441
_reflns_number_gt                14914
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.933
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'SMART (Bruker, 2002)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0800P)²]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.05(5)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         16441
_refine_ls_number_parameters     446
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.1301
_refine_ls_wR_factor_gt          0.1241
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N -0.0658(11) 0.5104(11) 0.0838(8) 0.035(4) Uani 1 1 d . . . . .
H8C H -0.0993 0.5593 0.0890 0.053 Uiso 1 1 calc R U . . .
H8B H -0.1180 0.4767 0.0546 0.053 Uiso 1 1 calc R U . . .
H8A H -0.0051 0.5174 0.0593 0.053 Uiso 1 1 calc R U . . .
O1 O -0.0907(8) 0.4611(7) 0.2811(6) 0.027(3) Uani 1 1 d . . . . .
H9 H -0.1465 0.4651 0.3043 0.041 Uiso 1 1 calc R U . . .
O2 O -0.2185(8) 0.5026(7) 0.1743(6) 0.021(2) Uani 1 1 d . . . . .
O3 O 0.4667(8) 0.4217(7) 0.0619(6) 0.023(2) Uani 1 1 d . . . . .
H1 H 0.5049 0.3844 0.0879 0.028 Uiso 1 1 calc R U . . .
C1 C -0.1241(12) 0.4813(8) 0.2066(8) 0.016(3) Uiso 1 1 d . . . . .
C2 C -0.0252(12) 0.4745(9) 0.1625(8) 0.021(3) Uiso 1 1 d . . . . .
H7 H -0.0130 0.4153 0.1542 0.025 Uiso 1 1 calc R U . . .
C3 C 0.0893(12) 0.5089(9) 0.2032(8) 0.019(3) Uiso 1 1 d . . . . .
H6A H 0.0837 0.5687 0.2050 0.022 Uiso 1 1 calc R U . . .
H6B H 0.1069 0.4888 0.2581 0.022 Uiso 1 1 calc R U . . .
C4 C 0.1860(11) 0.4859(8) 0.1627(8) 0.016(3) Uiso 1 1 d . . . . .
C5 C 0.2191(12) 0.4050(9) 0.1630(8) 0.018(3) Uiso 1 1 d . . . . .
H4 H 0.1795 0.3651 0.1870 0.022 Uiso 1 1 calc R U . . .
C6 C 0.3117(12) 0.3828(9) 0.1275(8) 0.022(3) Uiso 1 1 d . . . . .
H5 H 0.3320 0.3273 0.1246 0.026 Uiso 1 1 calc R U . . .
C7 C 0.3734(11) 0.4418(8) 0.0966(8) 0.015(2) Uiso 1 1 d . . . . .
C8 C 0.3413(12) 0.5230(8) 0.0961(8) 0.018(3) Uiso 1 1 d . . . . .
H2 H 0.3810 0.5631 0.0723 0.021 Uiso 1 1 calc R U . . .
C9 C 0.2502(12) 0.5437(9) 0.1310(8) 0.018(3) Uiso 1 1 d . . . . .
H3 H 0.2305 0.5994 0.1337 0.022 Uiso 1 1 calc R U . . .
N2 N 0.5691(9) 0.5288(7) 0.4346(7) 0.018(2) Uani 1 1 d . . . . .
H11A H 0.6444 0.5189 0.4549 0.027 Uiso 1 1 calc R U . . .
H11B H 0.5256 0.5144 0.4703 0.027 Uiso 1 1 calc R U . . .
H11C H 0.5593 0.5826 0.4234 0.027 Uiso 1 1 calc R U . . .
O4 O 0.5999(8) 0.4975(6) 0.2419(5) 0.019(2) Uani 1 1 d . . . . .
H10 H 0.6577 0.4961 0.2204 0.028 Uiso 1 1 calc R U . . .
O5 O 0.7270(8) 0.4633(6) 0.3490(5) 0.018(2) Uani 1 1 d . . . . .
O6 O 0.0425(9) 0.4681(7) 0.4733(6) 0.023(2) Uani 1 1 d . . . . .
H18 H 0.0003 0.4297 0.4530 0.028 Uiso 1 1 calc R U . . .
C10 C 0.6305(11) 0.4796(8) 0.3158(8) 0.015(2) Uiso 1 1 d . . . . .
C11 C 0.5328(11) 0.4804(8) 0.3609(7) 0.014(2) Uiso 1 1 d . . . . .
H12 H 0.5219 0.4232 0.3773 0.016 Uiso 1 1 calc R U . . .
C12 C 0.4168(11) 0.5093(8) 0.3143(8) 0.016(3) Uiso 1 1 d . . . . .
H13A H 0.4231 0.5673 0.3007 0.020 Uiso 1 1 calc R U . . .
H13B H 0.3982 0.4783 0.2645 0.020 Uiso 1 1 calc R U . . .
C13 C 0.3212(11) 0.4995(8) 0.3585(7) 0.012(2) Uiso 1 1 d . . . . .
C14 C 0.2610(12) 0.5643(8) 0.3809(8) 0.018(3) Uiso 1 1 d . . . . .
H16 H 0.2837 0.6177 0.3699 0.021 Uiso 1 1 calc R U . . .
C15 C 0.1674(12) 0.5547(9) 0.4193(8) 0.021(3) Uiso 1 1 d . . . . .
H17 H 0.1274 0.6003 0.4343 0.025 Uiso 1 1 calc R U . . .
C16 C 0.1360(11) 0.4766(8) 0.4342(8) 0.016(3) Uiso 1 1 d . . . . .
C17 C 0.1950(12) 0.4103(9) 0.4133(8) 0.018(3) Uiso 1 1 d . . . . .
H15 H 0.1728 0.3571 0.4252 0.022 Uiso 1 1 calc R U . . .
C18 C 0.2857(12) 0.4210(9) 0.3754(8) 0.021(3) Uiso 1 1 d . . . . .
H14 H 0.3247 0.3750 0.3604 0.025 Uiso 1 1 calc R U . . .
N3 N -0.0375(9) 0.5444(7) 0.5978(6) 0.017(2) Uani 1 1 d . . . . .
H26C H -0.0326 0.5970 0.6140 0.025 Uiso 1 1 calc R U . . .
H26A H -0.1104 0.5337 0.5722 0.025 Uiso 1 1 calc R U . . .
H26B H 0.0124 0.5357 0.5647 0.025 Uiso 1 1 calc R U . . .
O7 O -0.0844(8) 0.4620(7) 0.7814(6) 0.022(2) Uani 1 1 d . . . . .
H27 H -0.1408 0.4670 0.8039 0.034 Uiso 1 1 calc R U . . .
O8 O -0.1985(8) 0.5295(7) 0.6834(6) 0.020(2) Uani 1 1 d . . . . .
O9 O 0.4801(8) 0.4637(6) 0.5590(6) 0.023(2) Uani 1 1 d . . . . .
H19 H 0.5221 0.4253 0.5792 0.028 Uiso 1 1 calc R U . . .
C19 C -0.1080(11) 0.4965(8) 0.7121(7) 0.013(2) Uiso 1 1 d . . . . .
C20 C -0.0077(12) 0.4899(8) 0.6675(8) 0.017(3) Uiso 1 1 d . . . . .
H25 H -0.0048 0.4329 0.6482 0.020 Uiso 1 1 calc R U . . .
C21 C 0.1090(11) 0.5103(8) 0.7177(8) 0.017(3) Uiso 1 1 d . . . . .
H24A H 0.1091 0.5679 0.7342 0.020 Uiso 1 1 calc R U . . .
H24B H 0.1213 0.4765 0.7658 0.020 Uiso 1 1 calc R U . . .
C22 C 0.2056(11) 0.4967(8) 0.6752(8) 0.016(3) Uiso 1 1 d . . . . .
C23 C 0.2498(13) 0.4222(9) 0.6689(9) 0.022(3) Uiso 1 1 d . . . . .
H22 H 0.2169 0.3777 0.6915 0.027 Uiso 1 1 calc R U . . .
C24 C 0.3393(12) 0.4076(9) 0.6317(8) 0.021(3) Uiso 1 1 d . . . . .
H23 H 0.3673 0.3540 0.6280 0.025 Uiso 1 1 calc R U . . .
C25 C 0.3893(11) 0.4736(8) 0.5990(8) 0.016(3) Uiso 1 1 d . . . . .
C26 C 0.3451(12) 0.5514(8) 0.6037(8) 0.018(3) Uiso 1 1 d . . . . .
H20 H 0.3767 0.5961 0.5805 0.021 Uiso 1 1 calc R U . . .
C27 C 0.2542(12) 0.5627(8) 0.6426(8) 0.017(3) Uiso 1 1 d . . . . .
H21 H 0.2247 0.6157 0.6471 0.021 Uiso 1 1 calc R U . . .
N4 N 0.5795(9) 0.4565(8) 0.9372(7) 0.020(3) Uani 1 1 d . . . . .
H30B H 0.6230 0.4106 0.9431 0.030 Uiso 1 1 calc R U . . .
H30C H 0.5197 0.4505 0.9627 0.030 Uiso 1 1 calc R U . . .
H30A H 0.6234 0.4994 0.9578 0.030 Uiso 1 1 calc R U . . .
O10 O 0.6097(9) 0.5178(8) 0.7449(6) 0.027(2) Uani 1 1 d . . . . .
H29 H 0.6693 0.5260 0.7265 0.041 Uiso 1 1 calc R U . . .
O11 O 0.7344(8) 0.4680(7) 0.8484(6) 0.020(2) Uani 1 1 d . . . . .
O12 O 0.0394(8) 0.4601(6) 0.9643(6) 0.021(2) Uani 1 1 d . . . . .
H37 H 0.0017 0.4248 0.9376 0.025 Uiso 1 1 d R U . . .
C28 C 0.6382(13) 0.4873(9) 0.8158(9) 0.021(3) Uiso 1 1 d . . . . .
C29 C 0.5351(11) 0.4708(8) 0.8537(8) 0.017(3) Uiso 1 1 d . . . . .
H31 H 0.4991 0.4191 0.8308 0.020 Uiso 1 1 calc R U . . .
C30 C 0.4415(12) 0.5357(9) 0.8418(8) 0.020(3) Uiso 1 1 d . . . . .
H32A H 0.4740 0.5868 0.8668 0.024 Uiso 1 1 calc R U . . .
H32B H 0.4166 0.5461 0.7848 0.024 Uiso 1 1 calc R U . . .
C31 C 0.3386(11) 0.5121(8) 0.8756(8) 0.016(3) Uiso 1 1 d . . . . .
C32 C 0.2701(11) 0.5741(8) 0.9003(8) 0.017(3) Uiso 1 1 d . . . . .
H35 H 0.2936 0.6291 0.8980 0.020 Uiso 1 1 calc R U . . .
C33 C 0.1680(12) 0.5567(8) 0.9281(8) 0.019(3) Uiso 1 1 d . . . . .
H36 H 0.1211 0.5989 0.9419 0.023 Uiso 1 1 calc R U . . .
C34 C 0.1389(12) 0.4763(8) 0.9344(8) 0.017(3) Uiso 1 1 d . . . . .
C35 C 0.2061(11) 0.4143(8) 0.9131(7) 0.013(2) Uiso 1 1 d . . . . .
H34 H 0.1854 0.3593 0.9192 0.016 Uiso 1 1 calc R U . . .
C36 C 0.3030(12) 0.4323(9) 0.8829(8) 0.020(3) Uiso 1 1 d . . . . .
H33 H 0.3463 0.3893 0.8666 0.024 Uiso 1 1 calc R U . . .
O1W O 0.7694(8) 0.4576(7) 0.5172(6) 0.022(2) Uani 1 1 d . . . . .
H28A H 0.7976 0.4226 0.4801 0.026 Uiso 1 1 d R U . . .
H28B H 0.7458 0.4220 0.5559 0.026 Uiso 1 1 d R U . . .
I1 I 0.58074(8) 0.24963(6) -0.20515(6) 0.0266(2) Uani 1 1 d . . . . .
I2 I 0.44273(9) 0.20853(6) -0.09984(6) 0.0281(2) Uani 1 1 d . . . . .
I3 I 0.27868(9) 0.14707(7) 0.01904(6) 0.0262(2) Uani 1 1 d . . . . .
I4 I 0.13713(8) 0.18339(6) 0.15417(6) 0.0231(2) Uani 1 1 d . . . . .
I5 I 0.02001(8) 0.23309(6) 0.27005(6) 0.0237(2) Uani 1 1 d . . . . .
I6 I -0.12802(8) 0.28248(6) 0.42647(6) 0.0236(2) Uani 1 1 d . . . . .
I7 I 0.07272(8) 0.22872(6) 0.54553(5) 0.02051(19) Uani 1 1 d . . . . .
I8 I 0.26810(8) 0.18234(6) 0.66221(6) 0.0233(2) Uani 1 1 d . . . . .
I9 I 0.07446(8) 0.22258(6) 0.79187(6) 0.0242(2) Uani 1 1 d . . . . .
I10 I -0.06140(8) 0.25898(6) 0.90099(6) 0.0222(2) Uani 1 1 d . . . . .
I11 I 0.79378(8) 0.31598(6) 0.03250(5) 0.0216(2) Uani 1 1 d . . . . .
I12 I 0.65440(8) 0.28447(6) 0.18242(6) 0.0234(2) Uani 1 1 d . . . . .
I13 I 0.51549(8) 0.24767(6) 0.28783(6) 0.0235(2) Uani 1 1 d . . . . .
I14 I 0.35145(8) 0.19067(6) 0.42206(5) 0.0218(2) Uani 1 1 d . . . . .
I15 I 0.54713(8) 0.24972(6) 0.53429(5) 0.02109(19) Uani 1 1 d . . . . .
I16 I 0.74581(10) 0.30414(7) 0.65432(6) 0.0300(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.479(19) . ?
N1 H8C 0.9100 . ?
N1 H8B 0.9100 . ?
N1 H8A 0.9100 . ?
O1 C1 1.318(16) . ?
O1 H9 0.8400 . ?
O2 C1 1.204(16) . ?
O3 C7 1.397(15) . ?
O3 H1 0.8400 . ?
C1 C2 1.522(19) . ?
C2 C3 1.515(19) . ?
C2 H7 1.0000 . ?
C3 C4 1.503(18) . ?
C3 H6A 0.9900 . ?
C3 H6B 0.9900 . ?
C4 C5 1.389(18) . ?
C4 C9 1.396(19) . ?
C5 C6 1.406(19) . ?
C5 H4 0.9500 . ?
C6 C7 1.383(19) . ?
C6 H5 0.9500 . ?
C7 C8 1.391(19) . ?
C8 C9 1.378(19) . ?
C8 H2 0.9500 . ?
C9 H3 0.9500 . ?
N2 C11 1.497(16) . ?
N2 H11A 0.9100 . ?
N2 H11B 0.9100 . ?
N2 H11C 0.9100 . ?
O4 C10 1.297(16) . ?
O4 H10 0.8400 . ?
O5 C10 1.208(16) . ?
O6 C16 1.412(16) . ?
O6 H18 0.8400 . ?
C10 C11 1.516(18) . ?
C11 C12 1.530(17) . ?
C11 H12 1.0000 . ?
C12 C13 1.493(17) . ?
C12 H13A 0.9900 . ?
C12 H13B 0.9900 . ?
C13 C14 1.381(18) . ?
C13 C18 1.408(19) . ?
C14 C15 1.408(19) . ?
C14 H16 0.9500 . ?
C15 C16 1.379(19) . ?
C15 H17 0.9500 . ?
C16 C17 1.382(18) . ?
C17 C18 1.375(18) . ?
C17 H15 0.9500 . ?
C18 H14 0.9500 . ?
N3 C20 1.492(17) . ?
N3 H26C 0.9100 . ?
N3 H26A 0.9100 . ?
N3 H26B 0.9100 . ?
O7 C19 1.308(16) . ?
O7 H27 0.8400 . ?
O8 C19 1.220(16) . ?
O9 C25 1.397(15) . ?
O9 H19 0.8400 . ?
C19 C20 1.542(18) . ?
C20 C21 1.523(18) . ?
C20 H25 1.0000 . ?
C21 C22 1.493(18) . ?
C21 H24A 0.9900 . ?
C21 H24B 0.9900 . ?
C22 C23 1.347(19) . ?
C22 C27 1.398(18) . ?
C23 C24 1.364(19) . ?
C23 H22 0.9500 . ?
C24 C25 1.409(19) . ?
C24 H23 0.9500 . ?
C25 C26 1.393(19) . ?
C26 C27 1.390(18) . ?
C26 H20 0.9500 . ?
C27 H21 0.9500 . ?
N4 C29 1.460(17) . ?
N4 H30B 0.9100 . ?
N4 H30C 0.9100 . ?
N4 H30A 0.9100 . ?
O10 C28 1.310(17) . ?
O10 H29 0.8400 . ?
O11 C28 1.214(17) . ?
O12 C34 1.402(16) . ?
O12 H37 0.8200 . ?
C28 C29 1.518(19) . ?
C29 C30 1.527(19) . ?
C29 H31 1.0000 . ?
C30 C31 1.502(18) . ?
C30 H32A 0.9900 . ?
C30 H32B 0.9900 . ?
C31 C36 1.393(19) . ?
C31 C32 1.422(18) . ?
C32 C33 1.416(18) . ?
C32 H35 0.9500 . ?
C33 C34 1.378(19) . ?
C33 H36 0.9500 . ?
C34 C35 1.388(18) . ?
C35 C36 1.383(18) . ?
C35 H34 0.9500 . ?
C36 H33 0.9500 . ?
O1W H28A 0.9700 . ?
O1W H28B 0.9700 . ?
I1 I2 2.7587(15) . ?
I4 I5 2.7747(13) . ?
I6 I7 2.9686(13) . ?
I7 I8 2.8692(14) . ?
I9 I10 2.7743(13) . ?
I12 I13 2.7514(14) . ?
I14 I15 2.8933(13) . ?
I15 I16 2.9648(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 H8C 109.5 . . ?
C2 N1 H8B 109.5 . . ?
H8C N1 H8B 109.5 . . ?
C2 N1 H8A 109.5 . . ?
H8C N1 H8A 109.5 . . ?
H8B N1 H8A 109.5 . . ?
C1 O1 H9 109.5 . . ?
C7 O3 H1 109.5 . . ?
O2 C1 O1 127.2(13) . . ?
O2 C1 C2 121.8(12) . . ?
O1 C1 C2 111.0(12) . . ?
N1 C2 C3 112.6(12) . . ?
N1 C2 C1 106.7(11) . . ?
C3 C2 C1 116.5(12) . . ?
N1 C2 H7 106.9 . . ?
C3 C2 H7 106.9 . . ?
C1 C2 H7 106.9 . . ?
C4 C3 C2 112.6(11) . . ?
C4 C3 H6A 109.1 . . ?
C2 C3 H6A 109.1 . . ?
C4 C3 H6B 109.1 . . ?
C2 C3 H6B 109.1 . . ?
H6A C3 H6B 107.8 . . ?
C5 C4 C9 118.7(13) . . ?
C5 C4 C3 118.7(12) . . ?
C9 C4 C3 122.3(12) . . ?
C4 C5 C6 119.5(13) . . ?
C4 C5 H4 120.3 . . ?
C6 C5 H4 120.3 . . ?
C7 C6 C5 120.1(14) . . ?
C7 C6 H5 120.0 . . ?
C5 C6 H5 120.0 . . ?
C6 C7 C8 121.0(13) . . ?
C6 C7 O3 121.3(12) . . ?
C8 C7 O3 117.7(12) . . ?
C9 C8 C7 118.1(13) . . ?
C9 C8 H2 120.9 . . ?
C7 C8 H2 120.9 . . ?
C8 C9 C4 122.4(13) . . ?
C8 C9 H3 118.8 . . ?
C4 C9 H3 118.8 . . ?
C11 N2 H11A 109.5 . . ?
C11 N2 H11B 109.5 . . ?
H11A N2 H11B 109.5 . . ?
C11 N2 H11C 109.5 . . ?
H11A N2 H11C 109.5 . . ?
H11B N2 H11C 109.5 . . ?
C10 O4 H10 109.5 . . ?
C16 O6 H18 109.5 . . ?
O5 C10 O4 125.4(13) . . ?
O5 C10 C11 120.3(12) . . ?
O4 C10 C11 114.2(11) . . ?
N2 C11 C10 108.7(10) . . ?
N2 C11 C12 111.4(11) . . ?
C10 C11 C12 115.4(11) . . ?
N2 C11 H12 107.0 . . ?
C10 C11 H12 107.0 . . ?
C12 C11 H12 107.0 . . ?
C13 C12 C11 112.9(11) . . ?
C13 C12 H13A 109.0 . . ?
C11 C12 H13A 109.0 . . ?
C13 C12 H13B 109.0 . . ?
C11 C12 H13B 109.0 . . ?
H13A C12 H13B 107.8 . . ?
C14 C13 C18 117.4(12) . . ?
C14 C13 C12 123.0(12) . . ?
C18 C13 C12 119.5(12) . . ?
C13 C14 C15 122.9(13) . . ?
C13 C14 H16 118.6 . . ?
C15 C14 H16 118.6 . . ?
C16 C15 C14 117.3(13) . . ?
C16 C15 H17 121.3 . . ?
C14 C15 H17 121.3 . . ?
C15 C16 C17 121.3(13) . . ?
C15 C16 O6 116.6(12) . . ?
C17 C16 O6 122.0(12) . . ?
C18 C17 C16 120.4(13) . . ?
C18 C17 H15 119.8 . . ?
C16 C17 H15 119.8 . . ?
C17 C18 C13 120.6(13) . . ?
C17 C18 H14 119.7 . . ?
C13 C18 H14 119.7 . . ?
C20 N3 H26C 109.5 . . ?
C20 N3 H26A 109.5 . . ?
H26C N3 H26A 109.5 . . ?
C20 N3 H26B 109.5 . . ?
H26C N3 H26B 109.5 . . ?
H26A N3 H26B 109.5 . . ?
C19 O7 H27 109.5 . . ?
C25 O9 H19 109.5 . . ?
O8 C19 O7 125.8(12) . . ?
O8 C19 C20 122.0(12) . . ?
O7 C19 C20 112.3(11) . . ?
N3 C20 C21 112.1(11) . . ?
N3 C20 C19 106.1(10) . . ?
C21 C20 C19 113.7(11) . . ?
N3 C20 H25 108.3 . . ?
C21 C20 H25 108.3 . . ?
C19 C20 H25 108.3 . . ?
C22 C21 C20 112.6(11) . . ?
C22 C21 H24A 109.1 . . ?
C20 C21 H24A 109.1 . . ?
C22 C21 H24B 109.1 . . ?
C20 C21 H24B 109.1 . . ?
H24A C21 H24B 107.8 . . ?
C23 C22 C27 118.6(13) . . ?
C23 C22 C21 121.6(13) . . ?
C27 C22 C21 119.8(12) . . ?
C22 C23 C24 123.3(14) . . ?
C22 C23 H22 118.3 . . ?
C24 C23 H22 118.3 . . ?
C23 C24 C25 118.6(14) . . ?
C23 C24 H23 120.7 . . ?
C25 C24 H23 120.7 . . ?
C26 C25 O9 118.0(12) . . ?
C26 C25 C24 119.7(13) . . ?
O9 C25 C24 122.2(12) . . ?
C27 C26 C25 119.1(13) . . ?
C27 C26 H20 120.5 . . ?
C25 C26 H20 120.5 . . ?
C26 C27 C22 120.7(13) . . ?
C26 C27 H21 119.7 . . ?
C22 C27 H21 119.7 . . ?
C29 N4 H30B 109.5 . . ?
C29 N4 H30C 109.5 . . ?
H30B N4 H30C 109.5 . . ?
C29 N4 H30A 109.5 . . ?
H30B N4 H30A 109.5 . . ?
H30C N4 H30A 109.5 . . ?
C28 O10 H29 109.5 . . ?
C34 O12 H37 109.5 . . ?
O11 C28 O10 125.9(14) . . ?
O11 C28 C29 121.0(13) . . ?
O10 C28 C29 113.0(12) . . ?
N4 C29 C28 106.9(11) . . ?
N4 C29 C30 111.1(11) . . ?
C28 C29 C30 116.2(12) . . ?
N4 C29 H31 107.4 . . ?
C28 C29 H31 107.4 . . ?
C30 C29 H31 107.4 . . ?
C31 C30 C29 112.9(12) . . ?
C31 C30 H32A 109.0 . . ?
C29 C30 H32A 109.0 . . ?
C31 C30 H32B 109.0 . . ?
C29 C30 H32B 109.0 . . ?
H32A C30 H32B 107.8 . . ?
C36 C31 C32 116.8(12) . . ?
C36 C31 C30 124.2(12) . . ?
C32 C31 C30 119.0(12) . . ?
C33 C32 C31 122.1(13) . . ?
C33 C32 H35 119.0 . . ?
C31 C32 H35 119.0 . . ?
C34 C33 C32 117.7(13) . . ?
C34 C33 H36 121.1 . . ?
C32 C33 H36 121.1 . . ?
C33 C34 C35 121.4(13) . . ?
C33 C34 O12 117.0(12) . . ?
C35 C34 O12 121.6(12) . . ?
C36 C35 C34 120.2(12) . . ?
C36 C35 H34 119.9 . . ?
C34 C35 H34 119.9 . . ?
C35 C36 C31 121.7(13) . . ?
C35 C36 H33 119.2 . . ?
C31 C36 H33 119.2 . . ?
H28A O1W H28B 106.3 . . ?
I8 I7 I6 178.07(5) . . ?
I14 I15 I16 177.34(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 N1 8.9(19) . . . . ?
O1 C1 C2 N1 -171.3(13) . . . . ?
O2 C1 C2 C3 135.6(15) . . . . ?
O1 C1 C2 C3 -44.6(17) . . . . ?
N1 C2 C3 C4 -66.9(16) . . . . ?
C1 C2 C3 C4 169.4(12) . . . . ?
C2 C3 C4 C5 -67.2(17) . . . . ?
C2 C3 C4 C9 118.7(15) . . . . ?
C9 C4 C5 C6 -4(2) . . . . ?
C3 C4 C5 C6 -178.0(12) . . . . ?
C4 C5 C6 C7 4(2) . . . . ?
C5 C6 C7 C8 -4(2) . . . . ?
C5 C6 C7 O3 179.2(13) . . . . ?
C6 C7 C8 C9 4(2) . . . . ?
O3 C7 C8 C9 -179.2(12) . . . . ?
C7 C8 C9 C4 -4(2) . . . . ?
C5 C4 C9 C8 4(2) . . . . ?
C3 C4 C9 C8 177.9(13) . . . . ?
O5 C10 C11 N2 48.6(16) . . . . ?
O4 C10 C11 N2 -131.2(12) . . . . ?
O5 C10 C11 C12 174.6(12) . . . . ?
O4 C10 C11 C12 -5.2(17) . . . . ?
N2 C11 C12 C13 -62.2(14) . . . . ?
C10 C11 C12 C13 173.1(11) . . . . ?
C11 C12 C13 C14 116.2(14) . . . . ?
C11 C12 C13 C18 -67.0(16) . . . . ?
C18 C13 C14 C15 0(2) . . . . ?
C12 C13 C14 C15 176.9(13) . . . . ?
C13 C14 C15 C16 0(2) . . . . ?
C14 C15 C16 C17 1(2) . . . . ?
C14 C15 C16 O6 179.6(11) . . . . ?
C15 C16 C17 C18 -1(2) . . . . ?
O6 C16 C17 C18 -180.0(13) . . . . ?
C16 C17 C18 C13 1(2) . . . . ?
C14 C13 C18 C17 -1(2) . . . . ?
C12 C13 C18 C17 -177.5(12) . . . . ?
O8 C19 C20 N3 11.6(17) . . . . ?
O7 C19 C20 N3 -169.5(11) . . . . ?
O8 C19 C20 C21 135.3(14) . . . . ?
O7 C19 C20 C21 -45.9(16) . . . . ?
N3 C20 C21 C22 -64.5(15) . . . . ?
C19 C20 C21 C22 175.2(11) . . . . ?
C20 C21 C22 C23 -80.9(17) . . . . ?
C20 C21 C22 C27 100.8(15) . . . . ?
C27 C22 C23 C24 0(2) . . . . ?
C21 C22 C23 C24 -178.8(13) . . . . ?
C22 C23 C24 C25 1(2) . . . . ?
C23 C24 C25 C26 -1(2) . . . . ?
C23 C24 C25 O9 -179.1(13) . . . . ?
O9 C25 C26 C27 179.5(12) . . . . ?
C24 C25 C26 C27 2(2) . . . . ?
C25 C26 C27 C22 -1(2) . . . . ?
C23 C22 C27 C26 1(2) . . . . ?
C21 C22 C27 C26 179.2(12) . . . . ?
O11 C28 C29 N4 18.2(19) . . . . ?
O10 C28 C29 N4 -166.4(12) . . . . ?
O11 C28 C29 C30 142.8(14) . . . . ?
O10 C28 C29 C30 -41.8(18) . . . . ?
N4 C29 C30 C31 -62.0(16) . . . . ?
C28 C29 C30 C31 175.6(12) . . . . ?
C29 C30 C31 C36 -29(2) . . . . ?
C29 C30 C31 C32 152.9(12) . . . . ?
C36 C31 C32 C33 -2(2) . . . . ?
C30 C31 C32 C33 175.9(13) . . . . ?
C31 C32 C33 C34 3(2) . . . . ?
C32 C33 C34 C35 -1(2) . . . . ?
C32 C33 C34 O12 178.1(11) . . . . ?
C33 C34 C35 C36 -2(2) . . . . ?
O12 C34 C35 C36 179.2(12) . . . . ?
C34 C35 C36 C31 2(2) . . . . ?
C32 C31 C36 C35 0(2) . . . . ?
C30 C31 C36 C35 -178.7(13) . . . . ?

_refine_diff_density_max         1.381
_refine_diff_density_min         -1.410
_refine_diff_density_rms         0.199

_shelxl_version_number           2013-2

